#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/66/1506607.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1506607
loop_
_publ_author_name
'Koo, Bonsuk'
'McDonald, Frank E.'
_publ_section_title
;
 Synthesis of the branched C-glycoside substructure of altromycin B.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              3621
_journal_page_last               3624
_journal_paper_doi               10.1021/ol050975u
_journal_volume                  7
_journal_year                    2005
_chemical_formula_sum            'C16 H22 O7'
_chemical_formula_weight         326.34
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2807(5)
_cell_length_b                   12.6741(8)
_cell_length_c                   15.0669(9)
_cell_measurement_reflns_used    6957
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.94
_cell_measurement_theta_min      2.70
_cell_volume                     1581.28(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22205
_diffrn_reflns_theta_full        28.40
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3948
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0375
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0849
_reflns_number_gt                3592
_reflns_number_total             3948
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol050975usi20050429_070821.cif
_cod_data_source_block           bk021m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1506607
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C -0.07984(16) 0.43745(10) 0.36245(9) 0.0220(3) Uani 1 1 d .
C2 C 0.08741(15) 0.42827(10) 0.40829(9) 0.0197(3) Uani 1 1 d .
C3 C 0.02790(15) 0.39950(10) 0.50039(9) 0.0179(3) Uani 1 1 d .
H3 H -0.0007 0.3228 0.5004 0.022 Uiso 1 1 calc R
C4 C 0.05864(16) 0.37721(11) 0.65282(9) 0.0210(3) Uani 1 1 d .
H4 H 0.1260 0.4035 0.7033 0.025 Uiso 1 1 calc R
C5 C -0.11225(16) 0.42143(11) 0.66713(9) 0.0208(3) Uani 1 1 d .
H5 H -0.1646 0.3818 0.7167 0.025 Uiso 1 1 calc R
C6 C -0.22251(15) 0.41470(11) 0.58386(9) 0.0203(3) Uani 1 1 d .
H6 H -0.2481 0.3393 0.5702 0.024 Uiso 1 1 calc R
C7 C -0.12627(15) 0.46210(11) 0.50999(9) 0.0193(3) Uani 1 1 d .
H7 H -0.1007 0.5375 0.5237 0.023 Uiso 1 1 calc R
C8 C 0.18188(16) 0.53145(11) 0.40476(8) 0.0199(3) Uani 1 1 d .
C9 C 0.10991(18) 0.62842(11) 0.38843(10) 0.0274(3) Uani 1 1 d .
H9 H -0.0028 0.6319 0.3769 0.033 Uiso 1 1 calc R
C10 C 0.2001(2) 0.71969(12) 0.38872(11) 0.0332(4) Uani 1 1 d .
H10 H 0.1496 0.7856 0.3773 0.040 Uiso 1 1 calc R
C11 C 0.36385(18) 0.71541(12) 0.40560(11) 0.0313(3) Uani 1 1 d .
H11 H 0.4260 0.7784 0.4063 0.038 Uiso 1 1 calc R
C12 C 0.43682(18) 0.61950(13) 0.42139(11) 0.0315(3) Uani 1 1 d .
H12 H 0.5496 0.6165 0.4326 0.038 Uiso 1 1 calc R
C13 C 0.34658(17) 0.52758(11) 0.42107(10) 0.0257(3) Uani 1 1 d .
H13 H 0.3976 0.4617 0.4320 0.031 Uiso 1 1 calc R
C14 C 0.06634(19) 0.25753(11) 0.65608(10) 0.0296(3) Uani 1 1 d .
H14A H -0.0103 0.2280 0.6132 0.044 Uiso 1 1 calc R
H14B H 0.0385 0.2333 0.7159 0.044 Uiso 1 1 calc R
H14C H 0.1759 0.2342 0.6412 0.044 Uiso 1 1 calc R
C15 C -0.49128(17) 0.41074(12) 0.63613(11) 0.0320(4) Uani 1 1 d .
H15A H -0.5263 0.3563 0.5941 0.048 Uiso 1 1 calc R
H15B H -0.5829 0.4564 0.6509 0.048 Uiso 1 1 calc R
H15C H -0.4506 0.3771 0.6903 0.048 Uiso 1 1 calc R
O1 O -0.19900(11) 0.45388(8) 0.42224(6) 0.0236(2) Uani 1 1 d .
O2 O -0.10760(12) 0.42756(8) 0.28481(7) 0.0299(2) Uani 1 1 d .
O3 O 0.17370(13) 0.34293(7) 0.37326(6) 0.0241(2) Uani 1 1 d .
H3A H 0.2017 0.3568 0.3209 0.036 Uiso 1 1 calc R
O4 O 0.13120(10) 0.41838(7) 0.57222(6) 0.0203(2) Uani 1 1 d .
O5 O -0.09605(12) 0.52913(8) 0.69265(7) 0.0258(2) Uani 1 1 d .
H5A H -0.1829 0.5502 0.7153 0.039 Uiso 1 1 calc R
O6 O -0.36664(11) 0.47221(8) 0.59712(7) 0.0259(2) Uani 1 1 d .
O1S O 0.29587(15) 0.38119(11) 0.21481(7) 0.0405(3) Uani 1 1 d .
C1S C 0.2303(2) 0.33683(13) 0.13768(11) 0.0375(4) Uani 1 1 d .
H1S1 H 0.2724 0.2652 0.1299 0.056 Uiso 1 1 calc R
H1S2 H 0.2602 0.3800 0.0863 0.056 Uiso 1 1 calc R
H1S3 H 0.1124 0.3343 0.1429 0.056 Uiso 1 1 calc R
H1S H 0.390(2) 0.4027(15) 0.2100(12) 0.045 Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 C1 O1 121.76(13)
O2 C1 C2 126.69(13)
O1 C1 C2 111.48(11)
O3 C2 C3 108.97(10)
O3 C2 C8 112.81(10)
C3 C2 C8 113.87(10)
O3 C2 C1 110.22(11)
C3 C2 C1 97.77(10)
C8 C2 C1 112.21(10)
O4 C3 C7 110.65(10)
O4 C3 C2 117.87(10)
C7 C3 C2 103.65(10)
O4 C3 H3 108.1
C7 C3 H3 108.1
C2 C3 H3 108.1
O4 C4 C14 111.63(12)
O4 C4 C5 111.55(11)
C14 C4 C5 113.47(12)
O4 C4 H4 106.6
C14 C4 H4 106.6
C5 C4 H4 106.6
O5 C5 C4 107.49(11)
O5 C5 C6 109.02(11)
C4 C5 C6 114.06(11)
O5 C5 H5 108.7
C4 C5 H5 108.7
C6 C5 H5 108.7
O6 C6 C7 110.39(11)
O6 C6 C5 110.72(10)
C7 C6 C5 105.41(10)
O6 C6 H6 110.1
C7 C6 H6 110.1
C5 C6 H6 110.1
O1 C7 C6 115.25(10)
O1 C7 C3 103.01(10)
C6 C7 C3 108.12(11)
O1 C7 H7 110.1
C6 C7 H7 110.1
C3 C7 H7 110.1
C13 C8 C9 119.02(13)
C13 C8 C2 117.91(12)
C9 C8 C2 123.05(11)
C10 C9 C8 120.70(13)
C10 C9 H9 119.6
C8 C9 H9 119.6
C9 C10 C11 120.01(14)
C9 C10 H10 120.0
C11 C10 H10 120.0
C12 C11 C10 119.80(14)
C12 C11 H11 120.1
C10 C11 H11 120.1
C11 C12 C13 120.34(14)
C11 C12 H12 119.8
C13 C12 H12 119.8
C12 C13 C8 120.12(14)
C12 C13 H13 119.9
C8 C13 H13 119.9
C4 C14 H14A 109.5
C4 C14 H14B 109.5
H14A C14 H14B 109.5
C4 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
O6 C15 H15A 109.5
O6 C15 H15B 109.5
H15A C15 H15B 109.5
O6 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C1 O1 C7 108.30(10)
C2 O3 H3A 109.5
C3 O4 C4 109.40(9)
C5 O5 H5A 109.5
C6 O6 C15 112.92(10)
C1S O1S H1S 115.1(13)
O1S C1S H1S1 109.5
O1S C1S H1S2 109.5
H1S1 C1S H1S2 109.5
O1S C1S H1S3 109.5
H1S1 C1S H1S3 109.5
H1S2 C1S H1S3 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.1988(17)
C1 O1 1.3522(17)
C1 C2 1.5520(18)
C2 O3 1.3998(15)
C2 C3 1.5170(18)
C2 C8 1.5247(19)
C3 O4 1.4001(15)
C3 C7 1.5100(17)
C3 H3 1.0000
C4 O4 1.4519(15)
C4 C14 1.5190(19)
C4 C5 1.5372(19)
C4 H4 1.0000
C5 O5 1.4244(17)
C5 C6 1.5540(18)
C5 H5 1.0000
C6 O6 1.4126(16)
C6 C7 1.4949(18)
C6 H6 1.0000
C7 O1 1.4565(16)
C7 H7 1.0000
C8 C13 1.3867(19)
C8 C9 1.3878(19)
C9 C10 1.377(2)
C9 H9 0.9500
C10 C11 1.381(2)
C10 H10 0.9500
C11 C12 1.378(2)
C11 H11 0.9500
C12 C13 1.384(2)
C12 H12 0.9500
C13 H13 0.9500
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 O6 1.4205(17)
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
O3 H3A 0.8400
O5 H5A 0.8400
O1S C1S 1.4004(19)
O1S H1S 0.83(2)
C1S H1S1 0.9800
C1S H1S2 0.9800
C1S H1S3 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A O1S 0.84 1.81 2.6378(15) 170.3 .
O5 H5A O2 0.84 2.05 2.8725(14) 168.1 2_465
O1S H1S O5 0.83(2) 1.93(2) 2.7536(15) 172.0(18) 2_564
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O2 C1 C2 O3 -42.19(18)
O1 C1 C2 O3 134.88(11)
O2 C1 C2 C3 -155.76(13)
O1 C1 C2 C3 21.31(13)
O2 C1 C2 C8 84.45(17)
O1 C1 C2 C8 -98.48(12)
O3 C2 C3 O4 87.24(13)
C8 C2 C3 O4 -39.66(15)
C1 C2 C3 O4 -158.19(11)
O3 C2 C3 C7 -150.14(10)
C8 C2 C3 C7 82.95(13)
C1 C2 C3 C7 -35.58(12)
O4 C4 C5 O5 -72.42(13)
C14 C4 C5 O5 160.46(11)
O4 C4 C5 C6 48.57(16)
C14 C4 C5 C6 -78.55(15)
O5 C5 C6 O6 -50.00(14)
C4 C5 C6 O6 -170.13(11)
O5 C5 C6 C7 69.39(13)
C4 C5 C6 C7 -50.75(15)
O6 C6 C7 O1 -66.90(14)
C5 C6 C7 O1 173.49(10)
O6 C6 C7 C3 178.51(10)
C5 C6 C7 C3 58.90(13)
O4 C3 C7 O1 166.66(9)
C2 C3 C7 O1 39.38(12)
O4 C3 C7 C6 -70.92(13)
C2 C3 C7 C6 161.81(10)
O3 C2 C8 C13 -37.75(17)
C3 C2 C8 C13 87.13(15)
C1 C2 C8 C13 -162.97(12)
O3 C2 C8 C9 144.01(13)
C3 C2 C8 C9 -91.11(15)
C1 C2 C8 C9 18.79(18)
C13 C8 C9 C10 -0.3(2)
C2 C8 C9 C10 177.94(13)
C8 C9 C10 C11 -0.2(2)
C9 C10 C11 C12 0.5(3)
C10 C11 C12 C13 -0.5(2)
C11 C12 C13 C8 0.0(2)
C9 C8 C13 C12 0.3(2)
C2 C8 C13 C12 -177.98(12)
O2 C1 O1 C7 179.81(12)
C2 C1 O1 C7 2.57(14)
C6 C7 O1 C1 -143.38(11)
C3 C7 O1 C1 -25.88(12)
C7 C3 O4 C4 66.04(13)
C2 C3 O4 C4 -174.97(11)
C14 C4 O4 C3 73.95(13)
C5 C4 O4 C3 -54.16(14)
C7 C6 O6 C15 154.64(12)
C5 C6 O6 C15 -89.02(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21200024
